Synthesis and Antimicrobial Activity of Nitrobenzyl-oxy-phenol Derivatives

Abstract

Two hydroquinone derivatives were prepared and their antimicrobial activity evaluated. Their minimum inhibitory concentrations (MICs) were determined using a broth dilution method. Gentamycin and ciprofloxacin were used as reference antibiotics. The antimicrobial activity of 4-(benzyloxy)phenol (monobenzone) was also evaluated based on its structural similarity to the new compounds; activity was comparable to that of 3,5-dimethyl-4-((4-nitrobenzyl)oxy)phenol (4a). 2,3,5-Trimethyl-4-((4-nitrobenzyl)oxy)phenol (4b) exhibited the best antibacterial activity against both clinical isolates and type strain of Moraxella catarrhalis (M. catarrhalis), with a MIC value of 11 µM, comparable to ciprofloxacin 9 µM.

Brevinin-2 Drug Family—New Applied Peptide Candidates Against Methicillin-Resistant Staphylococcus aureus and Their Effects on Lys-7 Expression of Innate Immune Pathway DAF-2/DAF-16 in Caenorhabditis elegans

“…These AMPs also had a positive effect on the innate immunity system (DAF-2/DAF-16) in C. elegans. The mechanism of a peptide-dependent increase in survival rate should be further investigated with consideration of mutant worm strains [34,51].…”

“…To achieve this, we firstly established a MRSA-C. elegans model to identify the effects of MRSA on an individual level in nematode worms. We screened the effective antimicrobial peptides of the Brevinin-2 family that were able to extend the life span of MRSA-infected nematodes [30][31][32][33][34]. Finally, the association between Brevinin-2 family numbers and the DAF-2/DAF-16 pathway of C. elegans was verified by the lys-7 relative expression level (mRNA and protein).…”

Novel Benzothiazole Derivatives as Potential Anti-Quorum Sensing Agents for Managing Plant Bacterial Diseases: Synthesis, Antibacterial Activity Assessment, and SAR Study

“…The isopropanolamine unit is a unique building block widely used in the development of pharmaceutical and pesticide compounds, such as tebuconazole (antifungal agent), propranolol hydrochloride (antihypertensive drug), and nelfinavir (anti-HIV drug). − In particular, an isopropanolamine-decorated coumarin derivative (compound 3 ) exhibited satisfactory antibacterial activity and excellent anti-QS activity via the regulation of DSFs . Recent studies of the dioxybenzene structure suggest that it could serve as an important pharmacophore as well as a useful building block for pesticide and/or drug discovery. − Rational drug design based on these active pharmacophores could lead to the identification of new bactericidal candidates that function by regulating QS.…”

Equilibrium Solubility Determination and Correlation of Monobenzone in Fifteen Monosolvents at a Series of Temperatures

“…Phenol and phenolic derivatives always have diverse properties and higher acidities due to the existence of aromatic rings as starting materials for the manufacture of a series of chemicals and intermediates, that is, antioxidants, dyes, synthetic detergents, inhibitors, pesticides, and aspirin, that are closely related to our lives. − As a representative phenolic compound, monobenzone (C 13 H 12 O 2 , CAS no. 103-16-2, chemical name 4-benzyloxyphenol, molecular weight 200.23 g·mol –1 , structural formula shown in Figure ) is a monobenzyl ether of hydroquinone approved by FDA, possessing broad chemistry and bioactive properties similar to hydroquinone. ,− Since the 1970s, it has been extensively used for curing topical depigmentation of advanced vitiligo that is one of the most common dermatological disorders troubling up to 2% of the population around the world. ,− Compared with traditional hydrogen, monobenzone is little excitant and has a stable nature and strong stimulating effect. On the other hand, monobenzone also has an antibacterial effect against Moraxella catarrhalis.…”